(a) Write the structures of A and B in the following reactions:
(i) $C H_{3} C O C l H_{2}, P d - B a S O_{4} \to A H_{2} N - O H \to B$
(ii) $C H_{3} M g B R 1. C O_{2} - --- \to 2. H_{2} O^{+} A P C l_{5} \to B$
(B) Distinguish between:
(i) $C_{6} H_{5} - C O C H_{3}$ and $C_{6} H_{5} - C H O$
(ii) $C H_{3} C O O H$ and HCOOH
(c) Arrange the following in the increasing order of their boiling points:
$C H_{3} C H O, C H_{3} C O O H, C H_{3} C H_{2} O H$

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Solution

(a) (i) $C H_{3} C O C l H_{2}, P d - B a S O_{4} - -------- \to C H_{3} C O H H_{2} N - O H - ----- \to C H_{3} C = (N - O H) H$
(ii) $C H_{3} M g B r 2. H_{2} O - --- \to 1. C O_{2} C H_{3} C O O H P C l_{5} - -- \to C H_{3} C O C l$
(B) (i) Acetophenone, $C_{6} H_{5} - C O C H_{3}$
Benzaldehyde $C_{6} H_{6} - C H O$
(ii) $C H_{3} C O O H$ ,acetic acid and $H C O O H$ , propanoic acid
(c) $C H 3 H O < C H 3 C H 2 O H < C H 3 C O O H$

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\begin{matrix} C H_{3} C N & (i) S n C l_{2} - H C l - -------- \to (i i) H_{2} O A d i l . N a O H - ----- \to & B H e a t - -- \to & C ↓ H C N D \end{matrix}

C_{6} H_{5} - C H = C H - C O C H_{3}

C H_{3} C H_{2} C O O H

H C O O H

C H_{3} C H_{2} O H, C H_{3} C O C H_{3}, C H_{3} C O O H

\begin{matrix} C H_{3} C N & (i) S n C l_{2} - H C l - -------- \to (i i) H_{2} O A d i l . N a O H - ----- \to & B H e a t - -- \to & C ↓ H C N D \end{matrix}

C_{6} H_{5} - C H = C H - C O C H_{3}

C H_{3} C H_{2} C O O H

H C O O H

C H_{3} C H_{2} O H, C H_{3} C O C H_{3}, C H_{3} C O O H

Arrange the following compounds in increasing order of their boiling points.

CH₃CHO, CH₃CH₂OH, CH₃OCH₃, CH₃CH₂CH₃

(C_{6} H_{5} N_{2}^{+} C l^{-})

C u C N / K C N

(i i) H_{2} O

(i i i) C H_{3} C H_{2} O H

(i) C_{2} H_{5} N H_{2}, C_{2} H_{5} O H, (C H_{3})_{3} N

C H_{3} C H_{2} O H, C H_{3} C O C H_{3}, C H_{3} C O O H

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